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Synthesis and structural confirmation on selective N-alkylation of (Z)-5-((5-chloro- 1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues with their molecular docking studies

By: Sreenatha, Vasappanavara.
Contributor(s): Prasad, Karnam Jayarampillai Rajendra.
Publisher: New Delhi CSIR 2021Edition: Vol.60(B), Sep.Description: 1264-1271p.Subject(s): GENERAL CHEMISTRYOnline resources: Click here In: Indian journal of chemistry (Section B)Summary: In the present investigation, a series of novel (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues have been designed and synthesized in good yields with the objective of selective N-alkylation at thiazolidine 2,4-dione ring in competence with indole ring under basic conditions in the presence of aprotic solvent dimethylformamide (DMF). The newly synthesized compounds have been characterized by spectral data (IR, 1H and 13C NMR, NOE, NOESY, 1H-1H-COSY and LC-MS). Further, molecular docking and ADME studies have revealed that the newly synthesized compounds have very good docking score against antidiabetic and anti-inflammation activities (PPARy and COX-2) as compared with standard rosiglitazone.
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In the present investigation, a series of novel (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues have been designed and synthesized in good yields with the objective of selective N-alkylation at thiazolidine 2,4-dione ring in competence with indole ring under basic conditions in the presence of aprotic solvent dimethylformamide (DMF). The newly synthesized compounds have been characterized by spectral data (IR, 1H and 13C NMR, NOE, NOESY, 1H-1H-COSY and LC-MS). Further, molecular docking and ADME studies have revealed that the newly synthesized compounds have very good docking score against antidiabetic and anti-inflammation activities (PPARy and COX-2) as compared with standard rosiglitazone.

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